1. Technical Field
The present invention relates to radiation-curable compositions, preferably to flooring compositions that contain specific nonreactive additives that allow for the preparation of curable materials with desired chemical and physical properties. These nonreactive additives are not cured by exposure to radiation and do not react chemically with basic components of radiation-curable compositions. More specifically, the invention relates to radiation-curable biobased floor-covering coatings for concrete or asphalt tiles.
2. Description of the Related Art
Industrial floors are often made from concrete or asphalt tiles. Curable polymer compositions, such as epoxy, polyurethane, polyurea, and the like are often applied onto floors as protective coatings. In recent years, it became popular to protect industrial floors with radiation-curable coating materials since such coatings are strong and easy to apply.
Heretofore and still nowadays petrochemical-based raw materials remain central in the coating industry. However, due to the increasing concern about depletion of fossil reserves and greenhouse gas emissions, a large range of natural polymers and biobased plastics have been developed as ideal products to replace petroleum-based polymeric materials.
U.S. Pat. No. 3,931,075 issued on Jan. 6, 1976 to Trecker, et al, discloses amine derivatives of acrylated epoxidized soybean oil compounds that can be used by themselves or in combination with other materials to produce coatings, adhesives, or molding compositions cured by radiation.
U.S. Pat. No. 5,719,227 issued on Feb. 17, 1998 and U.S. Pat. No. 5,843,576 issued on Dec. 1, 1998 to Rosenberry, et al, describe a coating composition including a multifunctional polyurethane (meth)acrylate oligomer and floor coverings made with the coating composition and, more particularly, to radiation-curable coatings that have superior gloss retention and resistance to abrasion, gouging, and stain. It should be noted that the polyurethane fragments are incorporated directly into the crosslinked polymeric structure.
U.S. Pat. No. 8,211,967 issued on Jul. 3, 2012 to La Scala, et al, describes curable composite resins incorporating fatty acid monomers. In particular, biobased acrylated components were shown to enhance the stability, shelf life, flexibility, and strength of the composite resin. The resins incorporating methacrylated fatty acid monomers can be cured by electron beam irradiation to form a stiff and hard polymer (Example 30).
US Patent Application Publication No. 20100276059 issued on Nov. 4, 2010 by inventors D. Tian, et al, discloses a floor covering that includes a wear layer that contains a resin and a photoinitiator in which the composition of the wear layer is curable by radiation having the strongest wavelength in the UV range of 400 to 450 nm. The resin is selected from the group consisting of acrylated urethane resin, acrylated polyester resin, (meth)acrylate oligomers, (meth)acrylate monomers, N-vinyl amides, maleate esters, fumarate esters, epoxide resins, vinyl ethers, vinyl esters, allyl ethers, allyl esters, vinyl aromatics, maleimides and derivatives thereof, epoxy resins, propenyl ethers, oxetanes, lactones, thiols, unsaturated polyesters, unsaturated fatty acids, unsaturated oils, unsaturated waxes, and combinations thereof. The coating composition in the step of coating the substrate further comprises a biobased polyol crosslinker, and the photoinitiator is a cationic initiator. The gloss of the wear layer can be controlled by controlling the amount of flatting agent in the composition applied to the surface, the amount of power applied to the surface coated with the composition, or the temperature of the surface coated with the composition when the coated surface is subjected to UV radiation.
US Patent Application Publication No. 20110046257 published on Feb. 24, 2011 (inventors Webster, et al.) relates to a UV-curable coating formulation containing a siloxane-functional unsaturated polyester resin, vinyl ether functional diluents, and a photoinitiator. The invention further provides a method of preparing an article with a low surface-energy coating.
US Patent Application Publication No. 20120148833 published on Jun. 14, 2012 (inventors Cao, et al.) describes and claims colored radiation-curable coating compositions for a surface such as a concrete floor. The composition includes one or more acrylate monomers or oligomers having at least four crosslinkable double bonds, at least one photoinitiator, one or more fillers, and at least one pigment or dye. These coating compositions allow for application of coatings having a thickness of at least 0.10 mm (4 mil).
US Patent Application Publication No. 20120202909 published on Aug. 9, 2012 (inventor Chen) provides a novel UV-curable plant oil-based formulation for use on surfaces such as metal, wood, paper, textiles, and plastic. The UV-curable coating includes acrylated soybean oil, a hyperbranched acrylate, an optional adhesion promoter, and an optional renewable reactive diluent.
U.S. Pat. No. 8,420,710 issued on Apr. 16, 2013 to Tian, et al., discloses a radiation-curable biobased coating, such as a UV/EB-curable biobased coating, for flooring applications. The coating composition includes a biobased component comprising renewable and/or biobased materials. The biobased component is selected from the group consisting of a biobased resin, a biobased polyol acrylate, or a biobased polyol. The biobased component is blended with a coating formula. The coating formula includes at least one initiator. The radiation-curable biobased coating contains at least 5 wt. % of renewable materials or biobased content and may be used with a wide variety of flooring applications, such as linoleum, hardwood, laminate, cork, bamboo, resilient sheet, and tile. In this application, properties of the coatings are not disclosed and therefore their practical applicability cannot be assessed.
US Patent Application Publication No. 20130101847 published on Apr. 25, 2013 (inventors Cao, et al.) describes and claims radiation-curable coating compositions for application on surfaces such as a concrete floor. The composition includes at least one multifunctional monomer or oligomer, a polymer, at least one photoinitiator, and one or more tertiary amine compounds containing zero or one crosslinkable double bond. These coating compositions allow for application of at least 0.15 mm (6 mil) thickness of the coating composition.
US Patent Application Publication No. 20130230729 published on Sep. 5, 2013 (inventors Tian, et al.) discloses a coating composition and a floor product. The coating composition has a biobased component that includes urethane acrylate, vinyl ether, or polyester acrylate. The coating composition includes at least 5% by weight of renewable and/or biobased component. The coating composition is radiation curable and is formed by acrylating a biobased polyol acrylate and reacting the biobased polyol acrylate with polyisocyanate to form a biobased resin. The floor product includes a cellulosic substrate and a biobased coating applied to the cellulosic substrate.
US Patent Application Publication No. 201303094549 Published on Nov. 21, 2013 (inventors Vanderlip, et al.) relates to a radiation-curable composition comprising (a) from 1 to 99% by weight of a (meth)acrylated natural oil, which is the reaction product of an unsaturated natural oil with an unsaturated anhydride and a hydroxyl functional (meth)acrylate, and (b) from 1 to 99% by weight of a (meth)acrylated oligomer and/or monomer, and optionally an inert resin and/or filler, as well as their use for making inks and coatings. Inert resins are generally selected from hydrocarbon resins, acrylic resins, polyesters, chlorinated polyesters, rosin esters, phenolic resins, polyamides, styrene allyl alcohol copolymers, alkyd resins, polydiallylphthalate resins, cetonic resins, and plasticizers such as sucrose benzoate.
US Patent Application Publication No. 20130345383 A1, published on Dec. 26, 2013 (inventors Chen, et al.) describes UV-curable branched and hyperbranched oligomers and polymers that contain reactive derivatives of cashew nutshell oil, and epoxidized and/or acrylated components. The novel oligomers and polymers are suitable for use as an oil, lubricant, coating, adhesive, resin, or composite.
U.S. Pat. No. 6,960,619 issued to Figovsky, et al, on Nov. 1, 2005 discloses UV-curable liquid acrylic-based compositions (for sealing applications, which include, among other things, products of reaction of nonisocyanate urethane diols with metacrylic or acrylic anhydride).
An analogous solution in U.S. Pat. No. 7,329,773 issued to Stone, et al, on Feb. 12, 2008 discloses a process for producing carbamoyloxy (meth)acrylates that comprises transesterification of hydroxyalkyl carbamates with (meth)acrylate of formula CH2═CR29—COOR30, wherein R29 is hydrogen or methyl and R30 represents an alkyl group comprising from 1 to 8 carbon atoms, in the presence of an organotitanate, an organozirconate catalyst, or an organotin catalyst. The patent also describes the carbamoyloxy (meth)acrylates thereby obtained and their use in radiation curable compositions.
U.S. Pat. No. 7,989,553 issued to Birukov, et al, on Aug. 2, 2011 discloses an epoxy-amine composition modified with a nonreactive hydroxyalkyl urethane based on petroleum-derived raw materials. US Patent Application Publication No. 20120208967 issued on Aug. 16, 2013 by inventors Figovsky, et al, describes a hybrid epoxy-urethane-amine composition that comprises a nonreactive hydroxyalkyl urethane obtained from carbonated-epoxidized unsaturated fatty acid triglycerides and a primary monoamine.